Premium
Novel Condensed Thionated Bis(phosphonic) Acid Salts with a Rigid Naphthalene‐1,8‐diyl Backbone
Author(s) -
Kilian Petr,
Slawin Alexandra M. Z.,
Woollins J. Derek
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(199912)1999:12<2327::aid-ejic2327>3.0.co;2-b
Subject(s) - chemistry , naphthalene , salt (chemistry) , hydrolysis , derivative (finance) , medicinal chemistry , ring (chemistry) , proton nmr , stereochemistry , organic chemistry , financial economics , economics
New salts of thionated (naphthalene‐1,8‐diyl)bis(phosphonic) acid monoanhydrides [PPh 4 + ] 2 [C 10 H 6 PS 2 (μ‐S)PS 2 2– ] ( 2 ) and [K + ] 2 [C 10 H 6 PS 2 (μ‐S)POS 2– ]·H 2 O ( 3 ) both containing the C 3 P 2 S ring, were prepared in high yields by the reaction of 2,4‐(naphthalene‐1,8‐diyl)‐1,3,2,4‐dithiadiphosphetane 2,4‐disulfide ( 1 ) with NaHS and PPh 4 Cl, or KOH, respectively, in water. The derivative 3 , containing a P=O terminal bond as well as P–S–P bridge, undergoes, in acid conditions, a rearrangement reaction leading to the O,S‐symmetrically substituted derivative [K + ] 2 [C 10 H 6 PS 2 (μ‐O)PS 2 2– ] ( 4 ) containing a C 3 P 2 O heterocycle. Dipotassium salt 4 was converted into the bis(tetraphenylphosphonium) salt 5 by the treating with PPh 4 Cl. Hydrolysis of [PyH + ][C 10 H 6 P(S)(NHMe)(μ‐S)PS 2 2– ] ( 15 ) led to [CH 3 NH 3 + ][PyH + ][C 10 H 6 POS(μ‐O)POS 2– ]·1.5 Py ( 6 ). New compounds were characterised by 31 P{ 1 H}‐, 1 H‐ and 13 C{ 1 H}‐NMR, FT‐IR, ES‐MS and in the cases 2 – 6 by X‐ray structure determination. The 31 P{ 1 H}‐NMR spectra of these mixed O,S‐derivatives are briefly discussed.